Regioselective Synthesis of 5-Substituted 3-(β-d-Glycopyranosyl)isoxazoles and -isoxazolines by 1,3-Dipolar Cycloaddition as Potential Anticancer Agents and Glycogen Phosphorylase Inhibitors
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Open Access
- 22 August 2025
- journal article
- research article
- Published by MDPI AG in International Journal of Molecular Sciences
- Vol. 26 (17) , 8167
Abstract
Anhydro-aldose oximes were employed to generate in situ nitrile oxides via a halogenation/base-induced elimination sequence in the presence of NCS and Et3N, which were then used in 1,3-dipolar cycloadditions with alkenes and alkynes to afford 5-substituted 3-(β-d-glycopyranosyl)isoxazole and -isoxazoline derivatives exclusively. These newly synthesized glycomimetics were evaluated for their potential to act as antagonists of A2780 ovarian cancer cells and as inhibitors of glycogen phosphorylase; however, they exhibited no significant activity.Keywords
Funding Information
- National Research, Development and Innovation Office of Hungary (PD 142641, FK 132222, K142141, FK 146852, TKP2021-EGA, TKP2021-EGA-19, TKP2021-EGA-20)
- Bolyai Fellowship of the Hungarian Academy of Sciences (PD 142641, FK 132222, K142141, FK 146852, TKP2021-EGA, TKP2021-EGA-19, TKP2021-EGA-20)
- National Research, Development and Innovation Fund of Hungary (PD 142641, FK 132222, K142141, FK 146852, TKP2021-EGA, TKP2021-EGA-19, TKP2021-EGA-20)
- HUN-REN Hungarian Research Network (PD 142641, FK 132222, K142141, FK 146852, TKP2021-EGA, TKP2021-EGA-19, TKP2021-EGA-20)
- University of Debrecen Program for Scientific Publication (PD 142641, FK 132222, K142141, FK 146852, TKP2021-EGA, TKP2021-EGA-19, TKP2021-EGA-20)
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